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Literature DB >> 19552387

Stereoselective cross-coupling between allylic alcohols and aldimines.

Ivan L Lysenko¹, Hyung Goo Lee, Jin Kun Cha.

Abstract

A cross-coupling reaction between an allylic alcohol and an imine is described for stereoselective allylation of aromatic and aliphatic imines. This method provides operationally simple, enantioselective access to functionalized homoallylic amines. Particularly noteworthy is direct use of a functionalized allylic alcohol as an allylating reagent without prederivatization, which obviates the use of preformed organometallic reagents or activated imine derivatives.

Entities: Chemical Gene

Year: 2009 PMID： 19552387 PMCID： PMC2720054 DOI： 10.1021/ol901006c

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

21 in total

1. Indium-mediated asymmetric allylation of acylhydrazones using a chiral urea catalyst.

Authors: Kian L Tan; Eric N Jacobsen
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

2. Readily accessible, modular, and tuneable BINOL 3,3'-perfluoroalkylsulfones: highly efficient catalysts for enantioselective in-mediated imine allylation.

Authors: Robert Kargbo; Yoko Takahashi; Santosh Bhor; Gregory R Cook; Guy C Lloyd-Jones; Ian R Shepperson
Journal: J Am Chem Soc Date: 2007-03-13 Impact factor: 15.419

3. Allylsilane-vinylarene cross-metathesis enables a powerful approach to enantioselective imine allylation.

Authors: John D Huber; Nicholas R Perl; James L Leighton
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

4. Palladium-catalyzed allylation of imines with allyl alcohols.

Authors: Masamichi Shimizu; Masanari Kimura; Toshiya Watanabe; Yoshinao Tamaru
Journal: Org Lett Date: 2005-02-17 Impact factor: 6.005

5. Catalytic, enantioselective alkylation of alpha-imino esters: the synthesis of nonnatural alpha-amino acid derivatives.

Authors: Dana Ferraris; Brandon Young; Christopher Cox; Travis Dudding; William J Drury; Lev Ryzhkov; Andrew E Taggi; Thomas Lectka
Journal: J Am Chem Soc Date: 2002-01-09 Impact factor: 15.419

6. Conversion of allylic alcohols to stereodefined trisubstituted alkenes: a complementary process to the Claisen rearrangement.

Authors: Justin K Belardi; Glenn C Micalizio
Journal: J Am Chem Soc Date: 2008-12-17 Impact factor: 15.419

7. Zn-catalyzed asymmetric allylation for the synthesis of optically active allylglycine derivatives. Regio- and stereoselective formal alpha-addition of allylboronates to hydrazono esters.

Authors: Mari Fujita; Takashi Nagano; Uwe Schneider; Tomoaki Hamada; Chikako Ogawa; Shū Kobayashi
Journal: J Am Chem Soc Date: 2008-02-16 Impact factor: 15.419

8. Asymmetric allylboration of acyl imines catalyzed by chiral diols.

Authors: Sha Lou; Philip N Moquist; Scott E Schaus
Journal: J Am Chem Soc Date: 2007-11-17 Impact factor: 15.419

9. Chiral bis-pi-allylpalladium complex catalyzed asymmetric allylation of imines: enhancement of the enantioselectivity and chemical yield in the presence of water.

Authors: Rodney A Fernandes; Anton Stimac; Yoshinori Yamamoto
Journal: J Am Chem Soc Date: 2003-11-19 Impact factor: 15.419

10. Toward a versatile allylation reagent: practical, enantioselective allylation of acylhydrazones using strained silacycles.

Authors: Richard Berger; Philippe M A Rabbat; James L Leighton
Journal: J Am Chem Soc Date: 2003-08-13 Impact factor: 15.419

7 in total

1. Preparation of stereodefined homoallylic amines from the reductive cross-coupling of allylic alcohols with imines.

Authors: Ming Z Chen; Martin McLaughlin; Masayuki Takahashi; Michael A Tarselli; Dexi Yang; Shuhei Umemura; Glenn C Micalizio
Journal: J Org Chem Date: 2010-11-11 Impact factor: 4.354

2. Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors: Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal: Tetrahedron Date: 2016-09-07 Impact factor: 2.457

3. Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions.

Authors: Dexi Yang; Justin K Belardi; Glenn C Micalizio
Journal: Tetrahedron Lett Date: 2011-04-27 Impact factor: 2.415

4. Stereochemical lability of azatitanacyclopropanes: dynamic kinetic resolution in reductive cross-coupling reactions with allylic alcohols.

Authors: Dexi Yang; Glenn C Micalizio
Journal: Chem Commun (Camb) Date: 2013-10-09 Impact factor: 6.222